EP0555186A1 - Fungicidal compositions - Google Patents

Fungicidal compositions Download PDF

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Publication number
EP0555186A1
EP0555186A1 EP93810063A EP93810063A EP0555186A1 EP 0555186 A1 EP0555186 A1 EP 0555186A1 EP 93810063 A EP93810063 A EP 93810063A EP 93810063 A EP93810063 A EP 93810063A EP 0555186 A1 EP0555186 A1 EP 0555186A1
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EP
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Prior art keywords
wood
formula
compound
preserving
composition
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP93810063A
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German (de)
French (fr)
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EP0555186B1 (en
Inventor
Mark Daniel Mcdade
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Syngenta Participations AG
Original Assignee
Sandoz Erfindungen Verwaltungs GmbH
Sandoz AG
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Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B27—WORKING OR PRESERVING WOOD OR SIMILAR MATERIAL; NAILING OR STAPLING MACHINES IN GENERAL
    • B27K—PROCESSES, APPARATUS OR SELECTION OF SUBSTANCES FOR IMPREGNATING, STAINING, DYEING, BLEACHING OF WOOD OR SIMILAR MATERIALS, OR TREATING OF WOOD OR SIMILAR MATERIALS WITH PERMEANT LIQUIDS, NOT OTHERWISE PROVIDED FOR; CHEMICAL OR PHYSICAL TREATMENT OF CORK, CANE, REED, STRAW OR SIMILAR MATERIALS
    • B27K3/00—Impregnating wood, e.g. impregnation pretreatment, for example puncturing; Wood impregnation aids not directly involved in the impregnation process
    • B27K3/34—Organic impregnating agents
    • B27K3/38—Aromatic compounds
    • B27K3/40—Aromatic compounds halogenated
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B27—WORKING OR PRESERVING WOOD OR SIMILAR MATERIAL; NAILING OR STAPLING MACHINES IN GENERAL
    • B27K—PROCESSES, APPARATUS OR SELECTION OF SUBSTANCES FOR IMPREGNATING, STAINING, DYEING, BLEACHING OF WOOD OR SIMILAR MATERIALS, OR TREATING OF WOOD OR SIMILAR MATERIALS WITH PERMEANT LIQUIDS, NOT OTHERWISE PROVIDED FOR; CHEMICAL OR PHYSICAL TREATMENT OF CORK, CANE, REED, STRAW OR SIMILAR MATERIALS
    • B27K3/00—Impregnating wood, e.g. impregnation pretreatment, for example puncturing; Wood impregnation aids not directly involved in the impregnation process
    • B27K3/34—Organic impregnating agents
    • B27K3/343—Heterocyclic compounds

Definitions

  • This invention relates to a wood preservative composition and, more specifically, to a wood preservative composition containing a triazole fungicide as active ingredient.
  • Wood is an important resource material in the construction and industries. Wood can, however, be susceptible to mold, decay and discoloring due to fungal attack. Various compositions are known for combatting such fungal attacks, including certain triazole compounds such as those disclosed in European Patent Application 0 131 684.
  • A is selected from (i) and whereby the (3-carbon attaches to benzene ring of formula (I);
  • Wood refers to any type of wood material or wood product such as plywood, pressed wood, particle-board, wood chip, pulp or intermediates obtained in papermaking.
  • Particularly preferred compounds of the formula (I) are those in which R 1 is CI, R 2 and R 3 are H, R 4 is CH 3 and R 5 is cyclopropyl and A is the moiety (i) (commonly known as cyproconazole); those in which R 1 is Cl, R 2 is H, R 3 , R 4 and R 5 are CH 3 and A is the moiety (iii) (commonly known as tebuconazole); and those in which R 1 and R 2 are Cl, R 3 and R 4 are H, R 5 is ethyl and A is the moiety (ii) (commonly known as propiconazole).
  • compositions comprising a wood preserving orfungicidally effective amount of the compound of formula (I) and an environmentally acceptable carrier for such usage.
  • carrier means any environmentally acceptable liquid or solid material which may be added to the active constituent to bring it in an easier or improved applicable form, respectively to a usable or desirable strength of activity. It can for example be calcium, magnesium carbonate, xylene or water.
  • compositions may also be in the form of dispersible powders or granules and will conveniently comprise a surfactant, e.g. a wetting or dispersing agent to facilitate dispersion in liquids of the powder or granules which may contain also fillers and suspending agents.
  • a surfactant e.g. a wetting or dispersing agent to facilitate dispersion in liquids of the powder or granules which may contain also fillers and suspending agents.
  • aqueous dispersions or emulsions may be prepared by dissolving the active ingredient in an organic solvent optionally containing wetting, dispersing or emulsifying agents and then adding the mixture to water which may also contain one or more surfactants, such as wetting, dispersing or emulsifying agents.
  • Suitable organic solvents are ethylene dichloride, isopropyl alcohol, propylene glycol, diacetone alcohol, toluene, kerosene, methylnaphthalene, polyethyleneglycol, N-methyl-2-pyrrolidone, mixtures of C9 to C11 fatty alcohols, the xylenes, trichloroethylene, furfuryl alcohol, tetrahydrofurfuryl alcohol and glycol ethers.
  • compositions will be in the form of liquid preparations for use as dips or sprays which are generally aqueous dispersions or emulsions containing the active ingredient in the presence of one or more surfactants e.g. wetting agents, dispersing agents or emulsifying agents.
  • surfactants may be cationic, anionic or non-anionic, all of which are known in the art.
  • Suitable anionic agents are soaps, salts of aliphatic monoesters of sulphuric acid and salts of sulphonated aromatic compounds.
  • Suitable non-ionic agents are the condensation products of ethylene oxide with fatty alcohols or with alkyl phenols.
  • Other non-ionic agents are the partial esters derived from long chain fatty acids and hexitol anhydrides, the condensation products of partial esters with ethylene oxide and the lecithins.
  • compositions of the invention may contain further adjuvants including thickening agents, antifoam agents, antifreeze agents and suspending agents.
  • Suitable suspending agents are hydrophilic colloids and vegetable gums.
  • compositions for use as aqueous dispersions or emulsions are generally supplied in the form of a concentrate containing a high proportion of the active ingredient, the concentrate to be diluted with water before use.
  • the concentrates may conveniently contain up to 95%, suitably 10-85%, for example 25-60% by weight of the active ingredient.
  • aqueous preparations may contain varying amounts of the active ingredient depending upon the type of wood to be treated and the type of fungus, but typically the aqueous preparation will contain from 0.0001 % to 10% by weight active ingredient, more typically from 0.001% to 1 %.
  • formulations listed below are representative of suitable formulations for use in the invention, and are admixed and agitated in accordance with conventional methods to obtain a wood preservative composition.
  • Formulation 4 (wettable granule)
  • Suspensions containing a test compound of formula I are incorporated into potato dextrose agar (PDA) to produce a series of five concentrations containing 100 ppm, 10 ppm, 1 ppm, 0.1 ppm, 0.01 ppm resp. of active ingredients.
  • the thus obtained agar test compositions are poured into 9-cm petri dishes. After solidification of the medium, each dish is inoculated with a mycelial disc (5 mm diameter) taken from the periphery of actively growing colonies on PDA (three replicate dishes per isolate per concentration). After incubation (24°C in darkness, 5-14 days depending on the growth rate of the fungi), colony radii are measured. Percentage growth inhibition is calculated on the basis of treated control plates. The EC90 (effective concentration causing 90 % growth inhibition) is determined on the basis of dose-response curves.
  • the compounds of formula (I) are effective in combatting various type of fungi including the following fungi and the symptoms to which they lead.
  • the compounds cyproconazole, propiconazole and tebuconazole when tested against a variety of fungal diseases demonstrate particularly good activity against basidiomycetes including the fungi Coriolus versicolor, Poria placenta, Serpula lacrymans, Coniophora souna, Gloeophyllum trabeum, Lentinus lepideus and Trametes versicolor.
  • Cyproconazole is particularly effective against Poria placenta, Lentinus lepideus and Trametes versicolor.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • Forests & Forestry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Chemical And Physical Treatments For Wood And The Like (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

Wood preserving composition comprising a compound of formula I
Figure imga0001
wherein
A is selected from (i)
Figure imga0002
Figure imga0003
and (iii)
Figure imga0004
whereby the β-carbon attaches to benzene ring of formula (I) ;
  • R1 and R2 are independently H or Cl;
  • R3 and R4 are independently H or CH3 ; and
  • R5 is methyl, ethyl or cyclopropyl and method for preserving wood with the aid of a compound of formula (I).

Description

  • This invention relates to a wood preservative composition and, more specifically, to a wood preservative composition containing a triazole fungicide as active ingredient.
  • Wood is an important resource material in the construction and industries. Wood can, however, be susceptible to mold, decay and discoloring due to fungal attack. Various compositions are known for combatting such fungal attacks, including certain triazole compounds such as those disclosed in European Patent Application 0 131 684.
  • It has now been found that certain triazole compounds of the formula (I)
    Figure imgb0001
    wherein
  • A is selected from (i)
    Figure imgb0002
    and
    Figure imgb0003
    whereby the (3-carbon attaches to benzene ring of formula (I);
    • R1 and R2 are independently H or Cl;
    • R3 and R4 are independently H or CH3; and
    • R5 is methyl, ethyl or cyclopropyl
    • are particularly effective at combatting various fungi which are known to cause mold, decay and discoloration of wood.
  • Wood, as used herein, refers to any type of wood material or wood product such as plywood, pressed wood, particle-board, wood chip, pulp or intermediates obtained in papermaking.
  • Particularly preferred compounds of the formula (I) are those in which R1 is CI, R2 and R3 are H, R4 is CH3 and R5 is cyclopropyl and A is the moiety (i) (commonly known as cyproconazole); those in which R1 is Cl, R2 is H, R3, R4 and R5 are CH3 and A is the moiety (iii) (commonly known as tebuconazole); and those in which R1 and R2 are Cl, R3 and R4 are H, R5 is ethyl and A is the moiety (ii) (commonly known as propiconazole).
  • The specific compounds mentioned in the preceding paragraph are commercially available. Other compounds falling under the scope of formula (I) are obtainable according to procedures analogous to those known for preparing the commercially available compounds.
  • The compounds of formula (I) for use as wood preservatives are conveniently formulated into compositions comprising a wood preserving orfungicidally effective amount of the compound of formula (I) and an environmentally acceptable carrier for such usage.
  • The term carrier as used herein means any environmentally acceptable liquid or solid material which may be added to the active constituent to bring it in an easier or improved applicable form, respectively to a usable or desirable strength of activity. It can for example be calcium, magnesium carbonate, xylene or water.
  • The compositions may also be in the form of dispersible powders or granules and will conveniently comprise a surfactant, e.g. a wetting or dispersing agent to facilitate dispersion in liquids of the powder or granules which may contain also fillers and suspending agents.
  • The aqueous dispersions or emulsions may be prepared by dissolving the active ingredient in an organic solvent optionally containing wetting, dispersing or emulsifying agents and then adding the mixture to water which may also contain one or more surfactants, such as wetting, dispersing or emulsifying agents. Suitable organic solvents are ethylene dichloride, isopropyl alcohol, propylene glycol, diacetone alcohol, toluene, kerosene, methylnaphthalene, polyethyleneglycol, N-methyl-2-pyrrolidone, mixtures of C9 to C11 fatty alcohols, the xylenes, trichloroethylene, furfuryl alcohol, tetrahydrofurfuryl alcohol and glycol ethers.
  • Typically, the compositions will be in the form of liquid preparations for use as dips or sprays which are generally aqueous dispersions or emulsions containing the active ingredient in the presence of one or more surfactants e.g. wetting agents, dispersing agents or emulsifying agents. The surfactants may be cationic, anionic or non-anionic, all of which are known in the art.
  • Suitable anionic agents are soaps, salts of aliphatic monoesters of sulphuric acid and salts of sulphonated aromatic compounds.
  • Suitable non-ionic agents are the condensation products of ethylene oxide with fatty alcohols or with alkyl phenols. Other non-ionic agents are the partial esters derived from long chain fatty acids and hexitol anhydrides, the condensation products of partial esters with ethylene oxide and the lecithins.
  • The compositions of the invention may contain further adjuvants including thickening agents, antifoam agents, antifreeze agents and suspending agents.
  • Suitable suspending agents are hydrophilic colloids and vegetable gums.
  • The compositions for use as aqueous dispersions or emulsions are generally supplied in the form of a concentrate containing a high proportion of the active ingredient, the concentrate to be diluted with water before use. The concentrates may conveniently contain up to 95%, suitably 10-85%, for example 25-60% by weight of the active ingredient. After dilution to form aqueous preparations, such preparations may contain varying amounts of the active ingredient depending upon the type of wood to be treated and the type of fungus, but typically the aqueous preparation will contain from 0.0001 % to 10% by weight active ingredient, more typically from 0.001% to 1 %.
  • Methods of applying the compounds to the wood to be treated, such as spraying, dipping, by paint brush, etc., are known to those skilled in the art. Application can be repeated, as necessary.
  • The formulations listed below are representative of suitable formulations for use in the invention, and are admixed and agitated in accordance with conventional methods to obtain a wood preservative composition.
    • Formulation 1
    • 400 g/I cyproconazole
    • 55 nonionic polymeric emulsifier blend (e.g. polyalkylene glycol ether/polyoxyethylene alkylaryl ether blend)
    • 66 g/I antifreeze (e.g. 1,2 propanediol)
    • 3 g/I thickening agent (e.g. xanthane gum)
    • 1 g/I bactericide
    • 4 g/I antifoam agent (e.g. silicon)
    • balance water
      Figure imgb0004
      Figure imgb0005
    Formulation 4 (wettable granule)
    • 10 % cyproconazole
    • 15 % dispersing agent (e.g. sodium lignin sulfonate)
    • 75 % carrier (e.g. calcium magnesium carbonate)
    Test of activity against wood destroying fungi in vitro
  • Suspensions containing a test compound of formula I are incorporated into potato dextrose agar (PDA) to produce a series of five concentrations containing 100 ppm, 10 ppm, 1 ppm, 0.1 ppm, 0.01 ppm resp. of active ingredients. The thus obtained agar test compositions are poured into 9-cm petri dishes. After solidification of the medium, each dish is inoculated with a mycelial disc (5 mm diameter) taken from the periphery of actively growing colonies on PDA (three replicate dishes per isolate per concentration). After incubation (24°C in darkness, 5-14 days depending on the growth rate of the fungi), colony radii are measured. Percentage growth inhibition is calculated on the basis of treated control plates. The EC90 (effective concentration causing 90 % growth inhibition) is determined on the basis of dose-response curves.
  • The compounds of formula (I) are effective in combatting various type of fungi including the following fungi and the symptoms to which they lead.
    Figure imgb0006
    Figure imgb0007
    • Fungicidal activity
  • The compounds cyproconazole, propiconazole and tebuconazole when tested against a variety of fungal diseases demonstrate particularly good activity against basidiomycetes including the fungi Coriolus versicolor, Poria placenta, Serpula lacrymans, Coniophora puteana, Gloeophyllum trabeum, Lentinus lepideus and Trametes versicolor.
  • Cyproconazole is particularly effective against Poria placenta, Lentinus lepideus and Trametes versicolor.

Claims (5)

1. Awood preserving composition comprising a wood preserving effective amount of a compound of the formula (I)
Figure imgb0008
wherein
A is selected from (i)
Figure imgb0009
and
Figure imgb0010
whereby the β-carbon attaches to benzene ring of formula (I); the R1 and R2 are independently H or Cl;
R3 and R4 are independently H or CH3; and
R5 is methyl, ethyl or cyclopropyl; and an environmentally acceptable carrier.
2. The composition of Claim 1 wherein compound of formula I is selected from cyproconazole, propiconazole and tebuconazole.
3. The composition of Claim 2, wherein the compound of formula I is cyproconazole.
4. The composition of Claims 1 to 3 comprising additionally a surfactant.
5. A method for preserving wood comprising applying to the surface of said wood a wood preserving effective amount of the compound of Claims 1-3.
EP93810063A 1992-02-05 1993-02-02 Fungicidal compositions Expired - Lifetime EP0555186B1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB9202378 1992-02-05
GB929202378A GB9202378D0 (en) 1992-02-05 1992-02-05 Inventions relating to fungicidal compositions

Publications (2)

Publication Number Publication Date
EP0555186A1 true EP0555186A1 (en) 1993-08-11
EP0555186B1 EP0555186B1 (en) 1997-11-05

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US (1) US5874456A (en)
EP (1) EP0555186B1 (en)
JP (1) JP2766840B2 (en)
AT (1) ATE159885T1 (en)
AU (1) AU665800B2 (en)
CA (1) CA2088692C (en)
CH (1) CH686333A5 (en)
DE (1) DE4301885C2 (en)
DK (1) DK0555186T3 (en)
ES (1) ES2108250T3 (en)
FR (1) FR2687543B1 (en)
GB (2) GB9202378D0 (en)
GR (1) GR3025506T3 (en)
IT (1) IT1261173B (en)
MX (1) MX9300615A (en)
NZ (1) NZ245833A (en)
ZA (1) ZA93820B (en)

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EP0591764A1 (en) * 1992-10-05 1994-04-13 Bayer Ag Microbicidal agents
FR2802771A1 (en) * 1999-12-24 2001-06-29 Commissariat Energie Atomique New isocyanate-, anhydride- or epoxy-functionalized biocidal compounds, useful for grafting onto substrates, e.g. wood, to provide biocidal, e.g. insecticidal or fungicidal, activity
US6303616B1 (en) 1998-04-25 2001-10-16 Agrevo Uk Limited Wood treatment
US6558685B1 (en) 1998-07-28 2003-05-06 Dr. Wolman Gmbh Method for treating wood against the attack of harmful fungi
WO2005051081A1 (en) * 2003-11-26 2005-06-09 Syngenta Participations Ag Method for the protection of materials
WO2007031198A1 (en) * 2005-09-13 2007-03-22 Lanxess Deutschland Gmbh Use of triclosan for wood protection
EP2033520A1 (en) 2007-09-07 2009-03-11 Cognis IP Management GmbH Use of biocide compositions for wood preservation

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US6423732B1 (en) * 1992-02-04 2002-07-23 Syngenta Participations Ag Synergistic combinations of cyproconazole
CA2521872C (en) * 2003-04-09 2010-11-30 Osmose, Inc. Micronized wood preservative formulations
US8637089B2 (en) 2003-04-09 2014-01-28 Osmose, Inc. Micronized wood preservative formulations
US8747908B2 (en) 2003-04-09 2014-06-10 Osmose, Inc. Micronized wood preservative formulations
NZ544699A (en) * 2003-06-17 2009-11-27 Phibrowood Llc Particulate wood preservative and method for producing same
US20060075923A1 (en) * 2004-10-12 2006-04-13 Richardson H W Method of manufacture and treatment of wood with injectable particulate iron oxide
US20060062926A1 (en) * 2004-05-17 2006-03-23 Richardson H W Use of sub-micron copper salt particles in wood preservation
US7316738B2 (en) * 2004-10-08 2008-01-08 Phibro-Tech, Inc. Milled submicron chlorothalonil with narrow particle size distribution, and uses thereof
US20050252408A1 (en) 2004-05-17 2005-11-17 Richardson H W Particulate wood preservative and method for producing same
WO2006044218A2 (en) 2004-10-14 2006-04-27 Osmose, Inc. Micronized wood preservative formulations in organic carriers
DE602006002638D1 (en) * 2005-04-21 2008-10-23 Rohm & Haas Wood preservatives
JP2007022947A (en) * 2005-07-14 2007-02-01 Nippon Nohyaku Co Ltd Mold-proofing agent composition for under floor soil
US20070259016A1 (en) * 2006-05-05 2007-11-08 Hodge Robert L Method of treating crops with submicron chlorothalonil
EP2263456A1 (en) * 2009-06-18 2010-12-22 LANXESS Deutschland GmbH Azole compounds containing amidoalkylamine to protect technical materials
CN111202078B (en) * 2020-02-18 2022-04-19 中国林业科学研究院木材工业研究所 Water-based chemical agent for preventing and treating biological spoilage of ancient building wood components

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EP0050738A1 (en) * 1980-10-28 1982-05-05 BASF Aktiengesellschaft Wood-preserving agent
US4542146A (en) 1982-04-29 1985-09-17 Janssen Pharmaceutica N.V. Process for the protection of wood and coatings against deterioration by microorganisms
GB2136423A (en) 1983-03-04 1984-09-19 Sandoz Ltd Fungicidal 1h-azole-1-ethanol derivatives
EP0148526A1 (en) 1983-12-21 1985-07-17 Janssen Pharmaceutica N.V. Water-dilutable wood-preserving liquids
EP0287346A1 (en) 1987-04-16 1988-10-19 E.I. Du Pont De Nemours And Company Fungicide compositions
EP0458061A1 (en) * 1990-05-23 1991-11-27 DESOWAG GmbH Agent for preserving wood and wooden materials
EP0458060A1 (en) 1990-05-23 1991-11-27 DESOWAG GmbH Agent for preserving wood and wooden materials
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Cited By (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0591764A1 (en) * 1992-10-05 1994-04-13 Bayer Ag Microbicidal agents
EP0878281A2 (en) * 1992-10-05 1998-11-18 Bayer Ag Microbicidal agents
EP0884149A2 (en) * 1992-10-05 1998-12-16 Bayer Ag Microbicidal agents
EP0884150A2 (en) * 1992-10-05 1998-12-16 Bayer Ag Microbicidal agents
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GB9202378D0 (en) 1992-03-18
AU3282793A (en) 1993-08-12
GR3025506T3 (en) 1998-02-27
CA2088692C (en) 2005-01-18
CH686333A5 (en) 1996-03-15
DK0555186T3 (en) 1998-02-02
EP0555186B1 (en) 1997-11-05
ATE159885T1 (en) 1997-11-15
DE4301885A1 (en) 1994-06-09
ITRM930056A0 (en) 1993-02-03
US5874456A (en) 1999-02-23
FR2687543B1 (en) 1995-11-03
GB2263868B (en) 1996-04-03
JP2766840B2 (en) 1998-06-18
IT1261173B (en) 1996-05-09
AU665800B2 (en) 1996-01-18
GB9302026D0 (en) 1993-03-17
MX9300615A (en) 1993-09-01
FR2687543A1 (en) 1993-08-27
DE4301885C2 (en) 2003-10-16
CA2088692A1 (en) 1993-08-06
ES2108250T3 (en) 1997-12-16
ITRM930056A1 (en) 1994-08-03
NZ245833A (en) 1995-09-26
ZA93820B (en) 1994-08-05
JPH05255016A (en) 1993-10-05
GB2263868A (en) 1993-08-11

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